CN103356517B - Application of Scopariusins in preparation of antibacterial medicines - Google Patents
Application of Scopariusins in preparation of antibacterial medicines Download PDFInfo
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- CN103356517B CN103356517B CN201310337806.5A CN201310337806A CN103356517B CN 103356517 B CN103356517 B CN 103356517B CN 201310337806 A CN201310337806 A CN 201310337806A CN 103356517 B CN103356517 B CN 103356517B
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- scopariusins
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- medicines
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- antibacterial
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- 229930191324 scopariusin Natural products 0.000 title claims abstract description 27
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 17
- 239000003814 drug Substances 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 229940079593 drug Drugs 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 229940124350 antibacterial drug Drugs 0.000 claims description 6
- 241000588724 Escherichia coli Species 0.000 abstract description 3
- 241000191967 Staphylococcus aureus Species 0.000 abstract description 3
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- 201000007336 Cryptococcosis Diseases 0.000 abstract 1
- 241000221204 Cryptococcus neoformans Species 0.000 abstract 1
- 241000589540 Pseudomonas fluorescens Species 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 230000000452 restraining effect Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 241000554617 Isodon scoparius Species 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 230000003592 biomimetic effect Effects 0.000 description 3
- ZFYQTYYYCYTQSH-YWMUFLPLSA-N isoscoparin N Natural products COC(=O)C=C(/C)C[C@H](O)[C@@]1(C)[C@H](C)CCC2=C1CCCC2(C)C ZFYQTYYYCYTQSH-YWMUFLPLSA-N 0.000 description 3
- BDHATPNMGPTWJB-OAHLLOKOSA-N scopariusin A Natural products COC(=O)C=C(/C)CC1=C(C)[C@H](C)CCC2=C1CCCC2(C)C BDHATPNMGPTWJB-OAHLLOKOSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000009707 neogenesis Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 1
- YWMSSKBMOFPBDM-UHFFFAOYSA-N 4-carbamoylbenzenesulfonyl chloride Chemical compound NC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 YWMSSKBMOFPBDM-UHFFFAOYSA-N 0.000 description 1
- 229930183010 Amphotericin Natural products 0.000 description 1
- QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000711549 Hepacivirus C Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229960004821 amikacin Drugs 0.000 description 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
- 229960001656 amikacin sulfate Drugs 0.000 description 1
- 229940009444 amphotericin Drugs 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229960004130 itraconazole Drugs 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to an application of Scopariusins in preparation of antibacterial medicines, and belongs to the field of medicines. The Scopariusins has strong functions of restraining escherichia coli, pseudomonas fluorescens, staphylococcus aureus, proteusbacillus vulgaris and cryptococcus neoformans, and therefore the Scopariusins can be used as a compound with an antibacterial function, and is expected to be applied to the preparation of related medicines. The application of the Scopariusins in the preparation of the antibacterial medicines is firstly disclosed. The framework type is a brand-new framework type, and therefore the Scopariusins is impossibly revealed by other compounds. The Scopariusins has outstanding substantive characteristics. Meanwhile, the Scopariusins has significant progress in preventing and treating bacterial infection.
Description
Technical field
The present invention relates to the novelty teabag of compound S copariusins, particularly relate to Scopariusins and preparing the application in anti-bacterial drug.
Background technology
The health and lives of the mankind in the diffusion of pathogenic bacterium and the enhancing serious threat of drug resistance thereof, antibacterials are widely used in acquired immune deficiency syndrome (AIDS) as routine administration, organ transplantation and Chronic consumptions are (as cancer, diabetes, uremia etc.) treatment, although the antimicrobial agent used clinically is at present (as ketoconazole, amikacin, voriconazole, itraconazole, terbinafine, amphotericin etc.) better to the curative effect of skin and superficial place infection, but the cumulative toxicity of these antibacterials is stronger, usually cause lesions of liver and kidney, digestive tract stimulates, dizzy, irritated etc., so the novel antibacterial medicine finding mechanism of action uniqueness becomes one of focus of current medicament research and development.
The compound S copariusins that the present invention relates to is one and delivers (Min Zhou in 2013, et al., Scopariusins, A New Class of ent-Halimane Diterpenoids Isolated from Isodonscoparius, and Biomimetic Synthesis of Scopariusin A and Isoscoparin N.OrganicLetters, 2013, noval chemical compound 15(2): 314 – 317.), this compound has brand-new framework types, current purposes only relates to and suppresses hepatitis C virus (Min Zhou, et al., Scopariusins, A New Class ofent-Halimane Diterpenoids Isolated from Isodon scoparius, and Biomimetic Synthesisof Scopariusin A and Isoscoparin N.Organic Letters, 2013, 15(2): 314 – 317.), the Scopariusins that the present invention relates to belongs to first public preparing the purposes in anti-bacterial drug.
Summary of the invention
The object of the invention is to not find that it has the present situation of the report of antibacterial activity according in existing Scopariusins research, provide Scopariusins and preparing the application in anti-bacterial drug.
Described compound S copariusins structure is as shown in formula I:
Scopariusins has the effect of very strong suppression escherichia coli, fluorescent pseudomonas, Staphylococcus aureus, Bacillus proteus, neogenesis cryptococcus, so Scopariusins can be used as the compound with antibacterial action, and be expected to be applied in preparation antibacterials.
Scopariusins belongs to first public preparing the purposes in anti-bacterial drug, because framework types belongs to brand-new framework types, and it is unexpectedly strong for bacteriostatic activity, there is not the possibility being provided any enlightenment by other compounds, possess outstanding substantive distinguishing features, the control simultaneously for bacteriological infection obviously has significant progress.
Detailed description of the invention
The preparation method of compound S copariusins involved in the present invention is see document (Min Zhou, et al., Scopariusins, A New Class of ent-Halimane Diterpenoids Isolated from Isodonscoparius, and Biomimetic Synthesis of Scopariusin A and Isoscoparin N.OrganicLetters, 2013,15(2): 314 – 317.)
The present invention is further detailed explanation by the following examples, but protection scope of the present invention is not by any restriction of specific embodiment, but be limited by claim.
Embodiment 1: the preparation of compound S copariusins tablet involved in the present invention:
Get 5 g of compound Scopariusins, add 195 grams, dextrin, mixing, Conventional compression makes 1000.
Embodiment 2: the preparation of compound S copariusins capsule involved in the present invention:
Get 5 g of compound Scopariusins, add starch 195 grams, mixing, encapsulatedly makes 1000.
Its pharmaceutically active is further illustrated below by pharmacodynamic experiment.
Experimental example: Scopariusins antibacterial activity
Antibacterial activity test is the method adopting concentration dilution, and in triplicate, test pathogen has escherichia coli, fluorescent pseudomonas, Staphylococcus aureus, Bacillus proteus, neogenesis cryptococcus to each mensuration, and bacterial concentration is 105/mL.Scopariusins initial concentration is 50.0 μ g/mL(5% dimethyl sulfoxide DMSO), gradient dilution to 0.098 μ g/mL, the bacterium liquid of equivalent volumes and test sample Mixed culture are in 96 orifice plates, antibacterial culturing temperature is respectively 37 DEG C, observe after incubation time 24h, if find, when not having bacterium colony to be formed be sample lowest concentration of antimicrobial, i.e. MIC value.This experiment positive control is amikacin sulfate, and Scopariusins the anti-bacterial result is in table 1.
The table antibacterial MIC value of 1Scopariusins (μ g/mL)
Conclusion: Scopariusins has very strong antibacterial activity, and therefore Scopariusins of the present invention is expected to be used to prepare novel antibacterial medicine.
Claims (1)
1.Scopariusins is preparing the application in anti-bacterial drug, and described compound S copariusins structure is as shown in formula I:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310337806.5A CN103356517B (en) | 2013-08-05 | 2013-08-05 | Application of Scopariusins in preparation of antibacterial medicines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310337806.5A CN103356517B (en) | 2013-08-05 | 2013-08-05 | Application of Scopariusins in preparation of antibacterial medicines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103356517A CN103356517A (en) | 2013-10-23 |
| CN103356517B true CN103356517B (en) | 2015-04-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310337806.5A Active CN103356517B (en) | 2013-08-05 | 2013-08-05 | Application of Scopariusins in preparation of antibacterial medicines |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103356517B (en) |
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2013
- 2013-08-05 CN CN201310337806.5A patent/CN103356517B/en active Active
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| Publication number | Publication date |
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| CN103356517A (en) | 2013-10-23 |
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Effective date of registration: 20200219 Address after: 528448 Zhongshan, torch City, Guangdong, Hong Kong City, Kate residence 18, 1102 rooms. Co-patentee after: Wang Yayan Patentee after: Yang Jianbo Address before: 233000 Xianghe Home Floor No.9, Xinhuai Road, Dongsheng Street, Longzihu District, Bengbu City, Anhui Province Patentee before: Bengbu Qibang Science and Technology Information Consulting Co., Ltd. |